If you want to see the exact moment Juice became an underground hip-hop legend, all you have to do is download it. When the Chicago MC squared off against Eminem, who was still a couple years from filthy rich and famous, for the freestyle title at the 1997 Scribble Jam--an annual event that's sort of a cross between a hip-hop convention and a hip-hop World Cup--somebody was there to videotape it, and the footage is all over the Internet. (It's also included on a DVD released by the Scribble Jam folks.) Juice and Em's battle went for an unprecedented six overtime rounds. They took turns whipping up deadly disses off the tops of their heads, surrounded by a crowd of rabid hip-hop fiends who smelled blood. Em had already developed his trademark jittery, high-speed flow, but his machine-gun delivery and barrage of insults couldn't ruffle his cool, methodical opponent. Moving in for the kill, Juice held up Em's bottle of Bud and rapped, "Bitch, you do whatever I say, every rip." If you take the first letter of each word--and a couple liberties with spelling--that gives you "Budweiser."

Juice won that battle, but in the ten years since, he's had little luck translating his freestyle notoriety into record sales. He's put out a handful of albums, most recently All Bets Off in 2005, but none has made much of a splash. He says he's ghostwritten raps for major-label stars, but since he won't break the unwritten rule against naming names--that'd likely get him blacklisted--he can't parlay that work into a deal of his own. Skills alone won't make any rapper famous, except among the hardcore hip-hop faithful who cherish battle prowess over studio style--and since that audience isn't too impressed by an MC who just claims he's not reading preprepared lines in the booth, the few freestyle albums you'll find are almost always live battle recordings. Getting on the pop charts requires an undefinable combination of technique, production, personality, and timing that makes improvising entire verses look simple by comparison. Not even Supernatural, widely considered the best freestyler ever, has managed to make the leap. "There hasn't ever been a freestyle rapper who's made great records," says Juice, "other than Eminem."

Many hip-hop fans don't even have a clear idea what freestyling is. During the alleged freestyle segments on BET's Rap City, for instance, someone from a rapper's crew might jump on a mike and double the lines, making it obvious to any mildly attentive viewer that they're written in advance. As a consequence, Juice says, an audience sometimes doesn't realize he's improvising until he starts working in references to the room. "When I start talking about that brick wall and that girl's sick, y'all, then everybody believes it," he says. "But when I don't, people don't believe it."

Juice is still as hungry as he was when he battled Eminem, though, and he hasn't stopped hunting for the approach that'll translate into record sales--he says he's confident he can move the kind of numbers 50 Cent does. For his latest attempt, he's taking the possibly questionable route of releasing the least commercial-sounding music of his career. It might also be the best.

On his new DVD, Juice & the Machine: Live From the Party (available through banditproductions.com), he's surrounded not by a trash-talking battle crowd but by what looks like a bunch of jazz geeks. Or rather, they are jazz geeks, mostly. Juice's backing band came together last summer, when his manager and music director, Eric Sheinkop, threw himself a birthday party and decided to put together a group for the occasion that could improvise behind the MC. Sheinkop commissioned his friend Aaron Getsug, a young baritone saxophonist and AACM protege who's worked with Ernest Dawkins and David Boykin, to assemble the musicians--the Machine's original lineup also included keyboardist Brian Felix, drummer Brian Abraham, electric bassist Tim Lincoln, and a couple backup singers--and after only two rehearsals they were playing live in front of the cameras.

"I didn't handpick guys that I normally played with," Getsug says. "The band came together in a freak-of-nature way." The members share a background in jazz, though they also fuck around with rock, reggae, and IDM, among other things. "We all have different reference points," Felix says, "but can come together and communicate on a lot of different musical levels." The music on Live From the Party is a smoothly bumping jazz-funk fusion that invites comparisons to mid-90s jazz crossover experiments by the likes of Guru and the Digable Planets, but it's warmer, funkier, and more live sounding. The band runs frictionlessly--sometimes to a fault, slipping into a generic groove that wouldn't sound out of place coming from the ceiling speakers at Urban Outfitters.

Getsug and the Machine have been practicing like crazy to prepare for the release party at Metro this Friday, their first public show. In the six months since the DVD was recorded, they've become a much tighter, more responsive group. They're such a vital presence now, making audible connections between the improvising that happens in jazz and the improvising that happens in freestyling, that it's hardly right to call them a backing band anymore. "They pick it up so quick, it's like cogs moving," says Juice. "The way I look at it," Abraham says, "Juice is another soloist. He's another instrument."

The group has adapted some of the MC's old tracks and started writing original material with him. The two backup singers are gone, replaced by Russoul, a past winner of V103 and WGCI's Chicago Idol competition recruited by Juice. When I sat in on a rehearsal last week, Lincoln kicked off with a retro-funky R & B bass line and then the rest of the Machine jumped in, passing the lead between Getsug's sax and Felix's keyboard. They slipped into a heavy take on Dr. Dre's "The Next Episode" that Getsug transformed--with a blaring "Rump Shaker" sax solo--into Jay-Z's "Show Me What You Got." Russoul traded lines with Juice, matching the MC's freestyling with his own improvised melodies and lyrics--at one point he took my Reader business card and they both started riffing on it. I could feel everyone in the group pushing and pulling on everyone else, driving deeper into the groove. It didn't take much warming up before they were playing with enough heat to scorch the green band you'll see on the DVD.

Live-band improv isn't exactly mainstream in hip-hop, so it might seem strange for Juice to pin his crossover hopes on this project--but he has an answer for that. He thinks audiences have been "duped" by BET and Viacom to accept a dumbed-down version of hip-hop, and he wants to enlarge the mainstream the way OutKast did. "They were on some ghetto, southernplayalisticadillac shit, and then they took it to a higher level, and they brought their ghetto fans with them," he says. "That's my goal. That's why I want the Metro to be a mixed crowd--I want it to be a crowd that doesn't like real hip-hop, people who don't like real lyricism. So once we floor them, they'll come back, and they'll thirst for something greater."

I don't care to predict what the Metro crowd will go for, but watching Juice ride whatever his band threw at him, I understood that he'd solved one of his own biggest problems. What's been missing from his music, at least outside the freestyle circuit, is the same thing that made his battle with Eminem such a classic--someone who can give him a challenge to step up to.

For more on music, see our blogs Crickets and Post No Bills at chicagoreader.com.

Art accompanying story in printed newspaper (not available in this archive): photo/A. Jackson.